N-(4,4-Dimethoxybutyl)benzamid | 69001-40-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-(4,4-Dimethoxybutyl)benzamid
• 英文别名: N-(4,4-dimethoxybutyl)benzamide
• CAS: 69001-40-7
• 化学式: C₁₃H₁₉NO₃
• 分子量: 237.299
• InChiKey: WJCRTPNBHBMTQT-UHFFFAOYSA-N

物化性质

• 沸点：
  409.0±35.0 °C(Predicted)
• 密度：
  1.052±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  47.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  甲醇 、 (2-氨基苯基)-吡咯烷-1-甲酮 在 盐酸 、 copper(l) chloride 、 sodium nitrite 作用下， 以 水 为溶剂， 反应 48.0h， 以82%的产率得到N-(4,4-Dimethoxybutyl)benzamid
  参考文献：
  名称：

  一种方便的酰胺氧化合成方法

  摘要：

  在催化量的CuCl存在下，将邻氨基苯甲酰胺在甲醇中重氮化，可得到高产率的α-甲氧基苯甲酰胺。

  DOI：

  10.1016/s0040-4039(00)78191-3

文献信息

• Mitzlaff,M. et al., Justus Liebigs Annalen der Chemie, 1978, p. 1713 - 1733
  作者：Mitzlaff,M. et al.

  DOI：——

  日期：——
• One-Step RhCl₃-Catalyzed Deprotection of Acyclic <i>N</i>-Allyl Amides
  作者：Michael J. Zacuto、Feng Xu

  DOI：10.1021/jo070553t

  日期：2007.8.1

  [GRAPHICS]A convenient one-step RhCl3-catalyzed deprotection of acyclic N-allyl amides is described. Preliminary mechanistic studies reveal that the key to the success of the one-step deprotection process is the dual function of RhCl3 in alcohol solvents. Reaction of RhCl3 with n-PrOH not only provides an active rhodium hydride species to catalyze isomerization of N-allyl amides to corresponding enamides but also generates a crucial catalytic amount of HCl to convert the enamides to deallylated amides through N,O-acetal exchange.
• Exploratory Synthetic Studies of the α-Methoxylation of Amides <i>via</i> Cuprous Ion-Promoted Decomposition of <i>o</i>-Diazobenzamides
  作者：Gyoonhee Han、Matthew G. LaPorte、Mathias C. McIntosh、Steven M. Weinreb、Masood Parvez

  DOI：10.1021/jo961529a

  日期：1996.1.1

  A convenient nonelectrochemical amide oxidation method has been developed. The process involves a cuprous ion-promoted decomposition of o-diazobenzamides like 4, generated in situ from the corresponding o-aminobenzamides, to give N-acyliminium ion intermediate 9 via a 1,5-H-atom transfer, followed by metal-catalyzed oxidation of the resulting alpha-amidyl radical. The transformation produces alpha-methoxybenzamides 15 in good yields. An attempt was made to apply this oxidation method to a total synthesis of the alkaloid (-)-anisomycin (16). Scalemic o-aminobenzamide pyrrolidine derivatives 18a/18b underwent oxidation to give a-methoxylated amide substrates 19a/ 19b, respectively, in good yields. However, alkylation of the N-acyliminium intermediate 20 with (p-methoxybenzyl)magnesium chloride gave the undesired anti-compounds 22a/22b as the major products. The amide oxidation exhibits good regioselectivity with many unsymmetrical 2-substituted piperidine and pyrrolidine systems. In general, it appears that the larger the C-2 substituent, the greater the methylene/methine H-atom abstraction ratio. A mechanistic rationale for this selectivity is suggested based upon amide rotamer populations. An extension of this methodology can be used to conduct two sequential amide oxidations using readily prepared 2-amino-6-nitrobenzamides such as 68 and 69.